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Revision as of 13:02, 30 November 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit		Latest revision as of 16:12, 19 April 2024 edit undoFrietjes (talk | contribs)Autopatrolled, Extended confirmed users, Template editors1,002,398 edits update template syntax
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	{{cleanup|date=May 2008}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 399713412		| verifiedrevid = 399714633
⚫	| ImageFileL1 = Chloroformic acid.png
			| ImageFileL1 = Structural formula of chloroformic acid.svg
	| ImageSizeL1 = 110px		| ImageSizeL1 = 110
	| ImageNameL1 = Structural formula		| ImageAltL1 = Structural formula of chloroformic acid
	| ImageFileR1 = Chloroformic-acid-3D-balls.png
		⚫	| ImageFileR1 = Chloroformic acid 3D spacefill.png
	| ImageSizeR1 = 120px		| ImageSizeR1 = 110
	| ImageNameR1 = Ball-and-stick model
			| ImageAltR1 = Space-filling model of the chloroformic acid molecule
	| IUPACName = Carbonochloridic acid
			| PIN = Carbonochloridic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = 776–777 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
	| OtherNames = Chlorocarbonic acid		| OtherNames = Chloroformic acid<br />Chlorocarbonic acid
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 144299		| ChemSpiderID = 144299
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = AOGYCOYQMAVAFD-UHFFFAOYSA-N		| StdInChIKey = AOGYCOYQMAVAFD-UHFFFAOYSA-N
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo = 463-73-0		| CASNo = 463-73-0
	| PubChem = 164602		| PubChem = 164602
	| SMILES = ClC(=O)O		| SMILES = ClC(=O)O
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = CHClO<sub>2</sub>		| Formula = {{chem2|ClCO2H}}
			| H=1|Cl=1|C=1|O=2
	| MolarMass = 80.47 g/mol
	| Appearance =		| Appearance =
	| Density =		| Density =
			| MeltingPt = <!-- databases list 141 °C, but from the reaction of which it is claimed to be created, this seems like a chemial adjective or substring-match rather than the actual compound itself -->
	| MeltingPt =
	| BoilingPt =		| BoilingPt =
			| pKa = 0.27<ref name=metabolites>{{Cite web |url=https://hmdb.ca/metabolites/HMDB0250109 |title=Archived copy |access-date=2023-12-30 |archive-date=2023-12-10 |archive-url=https://web.archive.org/web/20231210184556/https://hmdb.ca/metabolites/HMDB0250109 |url-status=live }}</ref>
	| Solubility = }}		| Solubility =
⚫	| Section3 = {{Chembox Hazards
			| RefractIndex = }}
		⚫	|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| Autoignition = }}		| AutoignitionPt = }}
	}}		}}
	'''Chloroformic acid''' is an unstable ] with the formula ClC<sub></sub>O<sub>2</sub>H. It is the single acyl-halide derivative of ] (] is the double acyl-halide derivative). Chloroformic acid is also structurally related to ], which has a ] instead of the ]. Despite the similar name, it is very different from ].		'''Chloroformic acid''' is a ] with the formula {{chem2|ClCO2H|auto=1}}. It is the single acyl-halide derivative of ] (] is the double acyl-halide derivative). Chloroformic acid is also structurally related to ], in a way that the non-acidic ] of formic acid is replaced by ]. Despite the similar name, it is very different from ]. It is described as unstable.<ref>{{cite journal |doi=10.1021/cr60261a005 |title=Chemistry of Formic Acid and Its Simple Derivatives |date=1969 |last1=Gibson |first1=Harry W. |journal=Chemical Reviews |volume=69 |issue=5 |pages=673–692}}</ref>
⚫	Chloroformic acid itself is too unstable to be handled for chemical reactions. However, many ]s of this ] are stable and these ]s are important reagents in organic chemistry. They are used to prepare mixed ]s used in ]. Like other related halocarbons, it is a potentially dangerous ].
		⚫	Chloroformic acid itself is too unstable to be handled for chemical reactions. However, many ]s of this ] are stable and these ]s are important reagents in organic chemistry.<ref>{{cite journal |doi=10.1021/cr60232a004 |title=The Chemistry of Chloroformates |date=1964 |last1=Matzner |first1=Markus |last2=Kurkjy |first2=Raymond P. |last3=Cotter |first3=Robert J. |journal=Chemical Reviews |volume=64 |issue=6 |pages=645–687}}</ref> They are used to prepare mixed ]s used in ].
	Important chloroformate esters include ], ], ] and ].		Important chloroformate esters include ], ], ] and ].
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	==References==		==References==
			{{Reflist}}
	* {{cite web|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=742051
	| title = Chloroformic acid; Chlorocarbonic acid; Carbonochloridic acid|publisher=Dow Chemical|accessdate=20 May 2007}}
	* {{cite web|url=http://www.inchem.org/documents/pims/chemical/pim352.htm|title=Monochloroacetic Acid|publisher=IPCS Inchem|accessdate=20 May 2007}}
	{{DEFAULTSORT:Chloroformic Acid}}		{{DEFAULTSORT:Chloroformic Acid}}
	]		]
	]		]
	]